On Thu, 26 Jun 2025 at 12:43:12 +0000, mike travis wrote:
>  - the client trying to connect is a Debian 11 computer with putty. SSH 
> version is OpenSSH_8.4p1

If you're connecting from bullseye's putty then the client is putty
0.74-1+deb11u2.  Though I was also asking whether it works with OpenSSH
(openssh-client 8.4p1-5+deb11u5).

>  - At the stage when the error occurs, Open SSH is not active as disks are 
> still encrypted. Only Dropbear is running at this stage.

My question was whether it works with the OpenSSH *client* (and dropbear
2025.88-1 as server) and the same key material.

I am able to use ssh(1) from openssh-client 1:8.4p1-5+deb11u5 on a
bullseye system to connect to dropbear(8) from dropbear-bin 2025.88-1 on
a sid system, but I don't have a graphical bullseye system at hand to
try with putty.

Looking at the putty changelog [0] I see that 0.74 doesn't support
rsa-sha2-* (and that 0.75 through 0.81 have incorrect padding).

 * 0.75 (released 2021-05-08) Support for RSA key algorithms using SHA-2
   instead of SHA-1.
 * 0.82 (released 2024-11-27) Bug fix: SHA-2 based RSA signatures are
   now sent with correct zero padding.

Since 2025.87-1 dropbear is built without algorithms using SHA-1
following an upstream decision.  Quoting 
/usr/share/doc/dropbear-bin/changelog.Debian.gz

    dropbear (2025.87-1) unstable; urgency=low

      * New upstream release.  Highlights includes:
        […]
        + Due to vulnerabilities in the SHA-1 digest algorithm, dropbear(8) and
          dbclient(1) are now built without support for the ‘hmac-sha1’ 
integrity
          algorithm, ‘ssh-rsa’ key algorithm, and ‘diffie-hellman-group14-sha1’
          key exchange algorithm.  (The ‘diffie-hellman-group1-sha1’ key 
exchange
          algorithm, which also uses SHA-1, has been disabled at build time for
          dropbear(8) since 2018.76-1, but remains available to dbclient(1).)

          Note that OpenSSH has disabled support for these algorithms by default
          (runtime) since 8.8.  There is *no need* to rotate existing RSA host 
or
          user keys: OpenSSH has been supporting RFC8332 RSA/SHA-256/512
          signatures since 7.2, and dropbear since 2020.79.  However this change
          might break connection to legacy servers resp. from legacy clients.

It shouldn't yield at exception failure though.  Try booting with
'debug' in the kernel boot parameters (or alternatively by adding "-E"
to DROPBEAR_OPTIONS in /etc/dropbear/initramfs/dropbear.conf and
rebuilding the initramfs).  Do you see a "No matching algo hostkey"
error on the dropbear side before reaching the assertion failure?

-- 
Guilhem.

[0] https://www.chiark.greenend.org.uk/~sgtatham/putty/changes.html

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